An optically active 6-(3-aminopiperidin-1-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine derivative is known to be useful as a dipeptidylpeptidase inhibitor and an agent for the treatment of diabetes.
Patent Document 1 discloses a method of producing a 6-(3-aminopiperidin-1-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine derivative by reacting optically active 3-aminopiperidine with a 6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidine derivative.
Patent Document 2 discloses a method of efficiently producing an optically active 8-(3-aminopiperidin-1-yl)xanthine derivative by subjecting racemic 3-aminopiperidine to acylation with phthalic anhydride, subjecting the obtained 3-phthalimide piperidine to optical resolution with optically active tartaric acid, coupling the obtained optically resolved compound with a xanthine ring, and subjecting the obtained compound to deacylation.
Patent Document 3 discloses a method of optically resolving racemic piperidine-3-carboxamide with optically active lactic acid.
Patent Document 4 discloses a method of producing an optically active piperidine-3-carboxamide derivative by subjecting recemic piperidine-3-carboxamide to stereoselective hydrolysis with an enzyme derived from a microorganism, derivatizing the obtained optically active piperidine-3-carboxamide, and removing optically active nipecotic acid from the mixture.
In addition, the document also discloses a method of producing optically active 3-aminopiperidine by subjecting an optically active piperidine-3-carboxamide derivative to Hofmann rearrangement.
Non-Patent Document 1 discloses a method of producing an optically active nipecotate ester derivative by subjecting a tetrahydropyridinecarboxylate ester derivative to asymmetric reduction with a ruthenium complex.